Date of Award

Spring 1993

Document Type


Degree Name

Master of Science (MS)


Chemistry & Biochemistry



Committee Director

Frank E. Scully, Jr.

Committee Member

Charles E. Bell

Committee Member

Robert L. Ake

Call Number for Print

Special Collections LD4331.C45K43


Model solutions of the dipeptide glycylphenylalanine were chlorinated to five different chlorine-to-amino nitrogen (Cl/N) mole ratios and analyzed after 30 min by high performance liquid chromatography. At mole ratios of ≤ 1, N-chloroglycylphenylalanine (I) appeared to be the only major product. At a mole ratio ≤ 2, N, N-dichloroglycylphenylalanine (II) was the only product. Compound II decomposes in model solutions (t1/2= 6.4 hr) at pH 7.0 to form a compound tentatively identified as an H-chloroaldimine (III). Compound III in turn decomposes (t1/2= 36 hr) in model solutions at pH 7. o to (IV) . From 13C and 1H-NMR and IR, compound IV was identified as H-cyanoacylphenylalanine.

Glycyl-p_-['H]-phenylalanine (VI) was synthesized in order to monitor the reaction at low concentrations of the compound in a wastewater. A secondary wastewater (TKN = 1.29 mg/L; [NH3]= 0.074 mg/L) was inoculated with VI and chlorinated to nine different chlorine concentrations. The stabilities of the tritiated analogs of II and III in the wastewater were compared with those determined in model solutions.


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